Ossipee Holiday Rentals

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Holiday Rentals in Ossipee

Renovated waterfront home near skiing with lake view, 3 kayaks, dock & firepit
9.0 out of 10, Wonderful, (52)
"Great!"
Renovated waterfront home near skiing with lake view, 3 kayaks, dock & firepit
Lakefront & ski retreat with wrap-around deck, wood fireplace, & private beach
10.0 out of 10, Exceptional, (1)
Lakefront & ski retreat with wrap-around deck, wood fireplace, & private beach
Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski
10.0 out of 10, Exceptional, (148)
"Pool was certainly a hit with the children. Communication with owner was excellent as well as the response to issues raised. Owners should be very proud of this gem in Gilford!"
The price is NZ$4,097
per night
17 Jun - 18 Jun
Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski
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Dog-friendly A-frame with firepit, fireplace, AC, & kayaks - walk to the beach
9.4 out of 10, Exceptional, (70)
"We stayed in excellent VRBO rentals before. Only problem was garbage from previous rentals had never been removed from property. As snow melted we found an old cigar but on deck as well as dog poop. Which we picked up ourselves. The were many different conflicting instructions on what not to do and what to do in regards to heat, water, dishwasher (there is no dishwasher), but there were pods for one? Otherwise, we had fun. Would recommend streamlining instructions, and removing trash as we had...
Dog-friendly A-frame with firepit, fireplace, AC, & kayaks - walk to the beach
Newly Renovated Rustic Cabin
9.8 out of 10, Exceptional, (244)
"Nicely finished home with comfortable amenities. Suggest a deep clean and updated kitchenware. Comfortable beds."
Newly Renovated Rustic Cabin
Grand Blanc Mountain Home
9.8 out of 10, Exceptional, (82)
"Spacious, clean. Tons of games to play in their game room. Only down side is extremely spotty WiFi but that’s it. Other than that we had a wonderful time."
Grand Blanc Mountain Home
Vrbo Property
7.4 out of 10, Good, (3)
"Great lake access. The house was in a good location. The house needs a little TLC."
Vrbo Property
Fully renovated, dog-friendly home with private beach access & golf nearby
8.8 out of 10, Excellent, (3)
"Outdoor deck was not safe especially the steps leading to deck. The house was clean and exactly as it appeared on site. Not enough towels or toilet paper for 7 people. We had to run out and purchase toilet paper, only 2 already opened rolls were at property. Overall a beautiful place and neighborhood. Would definitely stay again."
Fully renovated, dog-friendly home with private beach access & golf nearby
Dog-friendly home with a pool table, washer/dryer, firepit & beach access
9.0 out of 10, Wonderful, (4)
"We stayed her with our five kids and a dog. The place had a great game room set away from the living room for our three teenage boys to hang out in and be boys. The girls had the living room so plenty of space when they needed a break from each other. It was pretty expensive tho. Figured it would be nice to have toilet paper, some dishwasher tabs, paper towels...basic stuff that most vrbo homes to start out with. All in all it good stay."
Dog-friendly home with a pool table, washer/dryer, firepit & beach access
Lakefront studio with private dock, fast WiFi & full kitchen - dog-friendly
10.0 out of 10, Exceptional, (23)
"We had an amazing stay. The cottage was nice and the view from the front deck was beautiful. My only criticism is They state towels provided however my husband and I were there for 10 days and there were only 4 bath towels. That is def not enough towels. If there was a washer dryer that would be fine but there is not. So we had to go and buy more towels. Other than that it was wonderful"
Lakefront studio with private dock, fast WiFi & full kitchen - dog-friendly
Million Dollar View of Lake Winnipesaukee!
9.8 out of 10, Exceptional, (32)
"We arrived to a clean, tidy and well appointed unit with an excellent view. The full kitchen is great for staying in, and the location near Meredith and Laconia gives plenty of dining options nearby"
Million Dollar View of Lake Winnipesaukee!
Amazing lakefront retreat with fireplace & stunning views - near skiing & golf
Amazing lakefront retreat with fireplace & stunning views - near skiing & golf
Easiest location! Rent a Boat, Attend a Wedding! 2600sqft on Main St Meredith
10.0 out of 10, Exceptional, (18)
"Chris was great. Home was great location and clean and so much room to spread out! Communication was amazing!"
Easiest location! Rent a Boat, Attend a Wedding! 2600sqft on Main St Meredith
Pet-friendly Waterfront Cottage: On-site Bunkhouse
3.5 star property
Pet-friendly Waterfront Cottage: On-site Bunkhouse
Lakefront home with private beach & dock - close to skiing
9.6 out of 10, Exceptional, (56)
"Peaceful, Clean and Outstanding views... Would highly recommend and will be back!!"
Lakefront home with private beach & dock - close to skiing
Custom Cottage Historic Meredith Village,walk to restaurants, shops Dog welcome
10.0 out of 10, Exceptional, (139)
"My husband and I enjoyed our stay at Meredith cottage. It was a perfect location to stores and restaurants. Also, close enough to lakefront park. Area was also dog friendly. We went on plenty of walks. Will come back to visit again."
The price is NZ$1,200
per night
27 Jun - 28 Jun
Custom Cottage Historic Meredith Village,walk to restaurants, shops Dog welcome
Lakeside home with water views, firepit, deck, fireplace, & W/D - dog-friendly
7.0 out of 10, Good, (2)
"Horrible infestation in the basement. A caterpillar was underneath my blanket & it’s hairs got stuck in my skin. Which caused burning, itching, hives $ prickling. My one year old also got some of the hair on him & broke out in hives. When I called customer service, the property manager never got back to me. There was no apology, no nothing. This property shouldn’t be rented out if there’s an infestation. Especially when young children are staying there. It’s been 2 days since the incident & my...
Lakeside home with water views, firepit, deck, fireplace, & W/D - dog-friendly
Lakefront condo with WiFi, private beach, full kitchen, & outdoor pool
7.6 out of 10, Good, (32)
"The s elk of cigarette smoke was off the charts, but then there weee the little thing d. Likescreen doo falling right off the rails. Klthu m"
Lakefront condo with WiFi, private beach, full kitchen, & outdoor pool
Lakefront home with views, water access for boating & swimming
8.8 out of 10, Excellent, (25)
"Wonderful and peaceful 4-day vacation. The place was clean, tidy, filled with all needed amenities, easily accessible and lovely lakeview from almost every window. We couldn't have asked for more. Great time and would visit again!"
Lakefront home with views, water access for boating & swimming
Spacious Belmont Home w/ Seasonal Pool & Grill!
9.0 out of 10, Wonderful, (59)
"Great house for my group. Quick easy access to Gunstock mountain. Extremely responsive owner. Hoping to return to this house again in the future."
Spacious Belmont Home w/ Seasonal Pool & Grill!
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Ossipee you may be interested in

Mill Falls at the Lake
3.0 star property
8.2 out of 10, Very good, (516)
"Having stayed here multiple times on the past. They have reduced the number of amenities in the rooms and past the cost of others to the guest as a resort fee. Other than these unexpected issues it's a great location with stunning views. "
The price is NZ$265
per night
25 Jun - 26 Jun
Mill Falls at the Lake
Fireside Inn & Suites Gilford
2.5 star property
8.8 out of 10, Excellent, (556)
"Clean easy access to the concert venue"
The price is NZ$250
per night
2 Jul - 3 Jul
Fireside Inn & Suites Gilford
Green Granite Inn, Ascend Hotel Collection
2.5 star property
7.4 out of 10, Good, (1393)
"Close to shopping"
The price is NZ$123
per night
9 Jun - 10 Jun
Green Granite Inn, Ascend Hotel Collection
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Ossipee holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Ossipee. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Ossipee. Seeing all the best attractions is bound to make you fall in love with Ossipee. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Ossipee short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Ossipee?

Yes, there are holiday rentals close to the most popular sights in Ossipee, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Ossipee has to offer?

Renovated waterfront home near skiing with lake view, 3 kayaks, dock & firepit: This holiday home rental outside of Ossipee is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of books.

How many holiday rentals are there in Ossipee?

With 6 Expedia holiday rentals, you're guaranteed to find just the right place for your Ossipee stay.

What’s there to see and do in Ossipee?

While exploring the area, visit family-friendly sights like Funspot Family Fun Center, or get outside and enjoy nature at Lake Winnipesaukee. In the wider area, you’ll find Ossipee Lake Trail and Lake Wentworth.

What’s a holiday rental in Ossipee like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Ossipee. Holiday rentals offer amenities such as hot tubs, fire pits and patios so your stay will be comfortable. If you're concerned about cleanliness, holiday rentals can provide a sense of security away from shared hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for families.

Recent reviews of Ossipee properties
Expedia verified reviews